The proliferation of available streaming video is increasing at exponential levels that will soon reach many billions if not trillions (or more) of such viewable streaming content. Content providers often provide free streaming video content to users in exchange for association of an advertisement with the video. For example, a pre-roll video advertisement is a short video advertisement that is automatically played before another video that has been selected for playing by a user. Another type of streaming video advertisement includes a mid-roll advertisement. A mid-roll advertisement is designed to play at some point within a video. Because a mid-roll video advertisement interrupts a user's viewing experience, the user often dismisses the original video at the time the mid-roll advertisement is played in order to avoid watching the mid-roll advertisement. Manually analyzing a video to strategically determine when to integrate a mid-roll video advertisement such that it does not prompt the user to prematurely dismiss the video can be difficult and time consuming.